HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Phenyl-2-pyridinamine | HCID 105097 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-(6-Chloro-5-methylpyridin-3-yl)acetic acid | HCID 55267357 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide | HCID 86657952 | — |
Reaction Steps
To a mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 74-4 (222 mg, 1.2 mmol), 5-phenylpyridin-2-amine (336 mg, 1.8 mmol) and HATU (684 mg, 1.8 mmol) in DMF (5 mL) was added DIEA (600 μL, 3.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 aqueous solution, water and brine, dried over Na2SO4, and concentrated by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in dichloromethane to give 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide 74-5 as dark yellow solid. MS m/z 356.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546396B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-336d3c77fa4946d091d6a920db7fbeea |
| Source note | uspto-grants-2013_10 |